


When I Get Horny

by Raicho



Category: Supernatural
Genre: Alpha/Beta/Omega Dynamics, Alternate Universe - College/University, Alternate Universe - Croatoan/Endverse, Anal Play, Anal Plug, Anal Sex, Belly Kink, Blow Jobs, Body Worship, Bondage, Bottom Dean, Butt Plugs, Candy, Chubby Dean, Coming Untouched, Costume Kink, Cursed Dean, Depression, Fallen Castiel, Finger Sucking, Fingerfucking, Future Fic, Hand Jobs, Homophobia, Human Castiel, John Winchester's A+ Parenting, Licking, Lollipops, M/M, Object Insertion, Omega Dean, One Shot, One Shot Collection, Orgasm, Pirates, Prostitution, Roleplay, Roommates, Rope Bondage, Sex Toys, Spitroasting, Suicidal Thoughts, Teenagers, Threesome, Vibrators, Virgin Dean, Weight Gain, Weight Issues
Language: English
Status: Completed
Published: 2014-01-04
Updated: 2015-07-21
Packaged: 2018-01-07 09:42:56
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 6
Words: 7,359
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1118398
Author URL: https://archiveofourown.org/users/Raicho/pseuds/Raicho
Summary: <blockquote class="userstuff">
              <p>A collection of short, kinky Supernatural one shots.</p>
            </blockquote>





	1. I Stain My Sheets

**Author's Note:**

> Endverse!Destiel + Fingerfucking

            He watched as Castiel exhaled into the open air, a trail of vapor-smoke streamed from his lips into the cold of the night. The ex-angel looked down at Dean with tender blue eyes and smiled as he crawled overtop the hunter; his body positioned between Dean’s widely parted legs.

            Dean watched as Castiel’s head bobbed up and down as he felt the wriggling fingers of Castiel’s hand explore the area of Dean’s pleasure centers. A slickened digit buried its way into Dean’s tight, pink channel, causing the hunter to clamp down tensely on the unexpected intrusion. A low moan leaked from the opening of Dean’s full lips and he could hear Castiel chuckle from above him.

            “Sshh.” The blue-eyed man soothed as he reached down and stuck another finger into the slick warmth.

            Dean nodded and relaxed himself enough to unclench his hold on Castiel’s instigation. He bit his bottom lip, hoping to contain any further moans and whining that may be subject to his expression.

            Once he regained his rather fragile composure, Dean opened his eyes and nodded his consent to Castiel. The mussed-haired man nodded in return, sliding his fingers further inside of Dean’s hole with slow movement. Dean felt the pressure of Castiel’s fingers separating and scissoring him open, the weight pressed against the rim of his entrance and he squirmed under pleasant touch.

            Gradually Castiel began to glide a third finger into the passage, and then another until Dean was pleasantly full. Gently, Castiel started pressing his fingers further into Dean’s channel before he retracted them away and toward the surface of Dean’s rim before they would sink back into the wet heat. With every cycle, Castiel would quicken his pace and slam into Dean with more enthusiasm and ferocity.

            Dean’s cock was rock solid and dripping as it slightly bobbed back and forth with the rhythm of Castiel’s motions. He could feel his heart racing and his bare nipples pebble at the brushing of cool air against his heated flesh.

            God, he felt like a stuff pig being charmingly tenderized before a splendid feast.

            “Cas!” Dean moaned as he panted heavily for breath.

            Cas cut his most current cycle of pounding short as he delicately retracted his fingers from inviting hollow of Dean’s used void. Dean could feel the trail of balmy lube dribble from his vacant crevice, spilling over his dimpled cheeks and onto the soiled navy blue sheets.

            Dean was pulled from his thoughts as he felt the ghosting tickle of Castiel’s breath on the head of his cock; the ex-angel’s lips hovered ever so close to the nearly-purple mushroom-shaped tip. Dean released another wanton moan of need.

            “Cas, gonna explode.”

            Dean heard the hearty, deep-throated and gravel-filled chuckle Castiel emitted before he felt the man’s solid hand drop over and sheath the length of Dean’s leaking member. Dean’s body shook with lewd sensations.

            Castiel diligently started stroking Dean in a matching rhythm to his previous thrusts; he greedily drank in the sight of Dean writhing on the floor beneath his touch. Without another thought, Castiel squeezed his unoccupied fingers back into the enveloping hospitality of Dean’s tunnel.

            “God, Cas, can’t hold it.”

            Castiel shushed the moaning man again, continuing on with his tempo. Dean reluctantly complied for another moment until he burst out screaming, ultimately breaking the tranquil silence of their cabin.

            With Dean’s erupting yowl, he clenched his eyes closed and tightened his grip on the rough sheets below him as he let himself go. Hot, sticky strings of cum gushed from the slit of Dean’s unyielding member, painting his belly in creamy white sweetness. As he rode down from his orgasmic high, he huffed in exhaustion while he smiled up at his blue-eyed lover.

            “Dammit, Cas,” the hunter gulped for air, “Got such big hands.”


	2. A Thing of Gossip

**Summary for the Chapter:**

> Vibrator + Virgin!Omega!Dean

**Notes for the Chapter:**

> Unbeta'd

            His finger flipped the switch as he gently lowered himself onto the length of the latex vibrator. He let the vibrations carry on as he worked to position himself against the motion ever so perfectly in hopes of catching that so often sought after high that most omegas his age claimed to crave.

            He’d heard the gossip in the grungy, confined walls of the high schools he’s wandered through since he’d hit puberty. He overheard how the alphas would talk about splitting open a virgin omega’s ass with their massively swelled knots and overflowing amounts of cum. He was present in the locker room when Tony started bragging to his other omega friends about how awesome his first time with Chase was; how the ecstasy was just out of this world.

            John had raised Dean to discourage sexual relations with alphas, he’d prefer that his son play the beta boyfriend for now as they moved from town to town hunting these damn ghosts every day of their pain-filled lives. Dean knew he wasn’t getting an alpha’s knot anytime soon; had known that since his first heat hit and his daddy didn’t even toss him a toy to appease his needs. John had always preached how Dean’s omega-ness was impure and a burden, how he should learn to suppress his urges and live in the ways of an honest man.

            _Fuck that logic_.

            The night John left for another hunt, Dean took the opportunity to sneak out to the nearest Adult-Mart to satisfy his needs. It seemed like there were plenty of people getting in on the omega-pussy-party, and Dean wanted in.

            He came back an hour later with a wide grin and a scrunched-up brown bag in his hands. Sam sat in the motel room with a questioning scowl aimed in the direction of the mystery bag, eventually asking Dean what he had purchased that was so necessary to cling to his chest.

            “None of your business, twerp.” Dean pushed his kid brother aside and strolled forward into the bedroom. Before he slammed the door on the approaching adolescent, he turned and gave his brother a stern glare, “Stay out, Sam.”

            “But, Dean…” Sam groaned as he stood still in his path, swaying his arms reluctantly at being told to stay out at Dean’s warning.

            “I mean it, Sam,” Dean glowered, “Just give me some time alone. Why don’t you go out with your geek friends for some pizza or something?”

            Sam’s mood perked up immediately at the approval of normalcy between him and the friends he longed to participate with. The boy nodded his head enthusiastically with agreement. Digging his fingers into his pocket, he excavated three crisp bills with Lincoln on the front and center and tossed the wad of folded paper to his brother. As Sam caught and pocketed the cash, Dean started rattling off about Sam’s curfew.

            “Yeah, I got it. Thanks, Dean!” Sam hollered from the motel entry, closing the door behind him.

            Dean sighed a breath of relief—finally he was alone and ready to do this.

            The young omega reached into the crumpled bag and pulled out the pink ribbed vibrator that sat perfectly in its packaged. He tore away at the plastic covering and smeared it with the newly purchased lube. He turned the vibrator on the ‘slow’ setting as he gripped the experimental object in his hand and watched it flick back and forth with fluid motion. He licked his lips, aroused at the thought of something moving inside of him like that.

            He turned the toy off again and ventured over toward his bed. He hastily stripped his pants and boxers off, tossing them carelessly in a heap on the floor beside the bed. He laid himself onto the mattress with his head supported by the soft down pillow. Fingering the vibrator in his hands, he then parted his legs and bent his knees, keeping his feet flat on the sheets. Slowly, he dipped his hand that held the toy downward until he felt it brush against the virgin skin of his scrotum. With a deep breath, Dean pushed the vibrator down, sliding it between and into the warm, moist folds of his pussy. He felt the pressure around the object’s insertion build as he lodged it further inward. When it was finally fitted snuggly, Dean stilled and took a moment to collect his thoughts.

             _Let’s see what you can do._

            Without another thought, Dean’s breath of courage egged him to flip the switch and ride out the sensation. As soon as the first pleasurable purr of rhythm coursed through his body, he felt the blooming hedonism inside of him begin to spark. Circuits were beginning to connect and electrical pulses buzzed just under the surface of his skin, wildly capturing him in the lascivious stirring that was centered in the pit of his loins.

            He pressed the object in further and hummed at the tension pulling at his taught flesh. His head fell backward onto the pillow and he moaned low and promiscuously. Short, breathy ‘mms’ and ‘ahs’ escaped from the confines of his plump lips, floating shamelessly on the stale air of the room.

            Another outburst of courage and equal curiosity ballooned and beckoned him to go deeper and harder. While burying it all the further inside, his index finger blindly roamed over the control and enabled the highest setting of vibration.

            Dean’s eyes instantly clenched tight as his mouth divided wide to let out a loud, needy moan. He clawed his free hand into the white cotton sheets and held on for dear life as the tremors caused his body to wrench and shake unwillingly.

             _Holy shit!_

            The pulsation continued for another few seconds until Dean had himself cumming all over the bed—smattering the bed set and his own shirt-covered belly. As the last droplets of creamy white leaked from his cock and pussy, Dean’s shaking hand fumbled for the switch and turned the vibrator off.

            His legs and arms were quivering with exhaustion and blissed-out stimulation from his first, real omega orgasm. Dean was left with his sweating back pressed into the sheets and his chest set in a harsh rise and fall motion to catch his breath. As he panted uncontrollably, his eyes unclenched and stared up to the water-stained ceiling above him. He blinked twice before he let out a slow, deep breath and started to chuckle.

            He raised himself into a sitting position and sat on the edge of the bed, aligning himself perfectly with the vanity mirror across the pathway. He watched his obscene reflection dimple with delight; he winked an eye and flopped onto his back.

             _Fuck John._

            Dean wasn’t giving this up anytime soon.


	3. A Pirate's Life

**Summary for the Chapter:**

> Pirate roleplay, butt plugs, rope bondage + Dean/Benny

**Notes for the Chapter:**

> For narimasha. Thanks for the lovely mermaid fic this morning. ~(˘▾˘~)  
> Beta'd by the lovely narimasha.

            The rush hour traffic had taken forever and a day (or so it seemed) to wait through before Benny pulled his truck into the front driveway of his newly purchased home. He pulled the keys from the ignition and slammed the metallic door before he briskly stepped down the driveway and over the steps to the pleasantly decorated front door. Benny fished his house key from his back pocket and turned the door open to display a comfortably inviting home.

            Stepping in and closing the door behind him as he shucked off his fall coat, he peeked around the front rooms of the house as he hollered aloud, “Baby, I’m home.”

            It wasn’t long before Benny was greeted with a sultry welcome from a very familiar voice.

            “Ahoy, matey.” Dean, Benny’s boyfriend and current housemate, winked as he stood at the top of the stairs wearing the most scandalous outfit possible.

            Benny had to do a double take to make sure he was seeing what was in front of him—Dean was dressed in black, skin-tight booty shorts that accentuated every possible curve of his lower half. His upper chest was covered with a red and black striped V-neck midriff top that cut off exactly eight inches above his navel. His legs were covered with black leather thigh-high boots, and his blonde head donned a black tricorn that was decorated with a white decorative feather that fluttered at its full height. Dean was also wielding a plastic cutlass in his right hand that he started to swing back and forth as he descended the stairs.

            “Well I’ll be damned.” Benny breathed as he watched the vision of lust saunter closer and closer.

            Dean grinned when he reached the bottom and flung his arms out around his boyfriend’s thick neck. He leaned his face upwards as he clung lazily onto the taller man, “Hello to you, too, captain.”

            “And what do I owe this fine pleasure to, lad?” Benny ducked his head for a kiss with Dean’s soft pink lips.

            Chuckling slightly, Dean answered, “Y’know it’s Halloween tomorrow,” Dean watched as Benny raised his brows in question, “And I know we’re already going to Sam’s party n’ all...” Dean loosened his hold around the man’s neck and dragged himself into a full standing position, “But I was thinking the two of us could have some fun beforehand?”

            Benny’s cock twitched at the idea, excited that Dean was so smart and thoughtful when it came to their needs, “You sure do know how to surprise a guy.”

            Dean kissed the scruff of Benny’s chin and tugged the front fabric of his shirt, trying to lead him upstairs, “How about we take this up to the crow’s nest, eh?”

            “Aye, aye, babe.” Benny smiled and eagerly climbed the stairs behind his boyfriend’s tight little ass.

            Once they were in the bedroom, Dean excitedly bounced onto the mattress and arranged himself tantalizingly across the black velvet covers. He watched hungrily as Benny approached the end of the bed and crawled past the storage bench that they kept at the foot. The lustful man slithered overtop Dean’s partially spread legs and towered over his midsection.

            “Where should I start first?” Benny purred as he looked over the tempting body that lay spread out beneath him.

            “Wherever you’d like, bucko.” Dean teased, pushing his knee up into Benny’s chest ever so delicately.

            Without further indication as to what he would do, Benny’s hands hastily dipped below Dean’s backside and slid the skin-tight shorts below his cheeks, pulling them below his knees.

            As Benny was pulling his only lower layer of covering from its place, Dean breathed, “Got some rope for you, too, captain.” Dean’s eyes roamed over to the nightstand drawer to Benny’s right.

            Benny curiously shifted his attention to the piece of furniture and tugged the small drawer open. He dropped his hand into the drawer and extracted a small binding of soft rope.

            Grinning at Dean, Benny swiftly pried Dean’s shirt from his chest and tossed it to the side of the bed. He took the rope and began to adeptly tie Dean into a pentagram knot. When Benny was finished and Dean’s arms were wrapped behind his back, the older man had Dean turn onto his stomach with his ass in the air.

            “Can’t wait to get me a piece of this booty.” Benny laughed as he placed his meaty palms atop the supple curve of Dean’s perfectly rounded globes.

            Clearing his throat and aiming his attention again toward the nightstand, Dean spoke, “There’s another surprise in there for you.”

            “Ain’t you just full of ‘em today?” Benny chortled as he once again reached over into the drawer and fished for Dean’s surprise. When his fingers grazed along the contour of cool steel, he curled his fingers and plucked the unknown object from its holding bin.

            When Benny opened his palm, it was to reveal a golden egg-shaped plug with an ornamental ruby at the base of its straightened tail. He held the plug for a moment before he looked back to Dean for further instruction.

            “This what I think it is?” Beny held the object in Dean’s view.

            “You know it is.”

            “Damn, sugah, you know how to hit the spot.” Benny’s cock began tenting his constricting pants.

            “Shut up n’ hit my spot, yeah?” Dean turned his head back and rested it on the pillow as he waved his ass in the air.

            Benny got the hint and stuck his tongue out to lick the tip of the egg, slickening it with his own spit before he directed the crown into the flexible entrance of Dean’s hole. Dean felt his skin pebble with goosebumps when the cool surface of the metallic object brushed against his bare skin, and he slowly released a low groan as the older man gently pressed the object further in.

            “Gonna bury my treasure inside your nice warm cave, darlin’.” Benny purred as he wriggled and pushed, watching Dean’s hole obscenely expand around the intruding gadget—his rim stretched taut and pink with the pressure.

            Dean moaned into the pillow as Benny finally shoved the plug in its full length; the base of the ruby gemstone was rested flush atop the entrance to Dean’s channel. Benny proceeded to massage the flesh of Dean’s ass, kneading it wantonly with his knuckles and finger pads. When he was finished massaging, Benny flipped Dean over onto his back so that he was stomach up and facing him again.

            “How’re you holdin’ up?” Benny asked.

            “Fuckin’ gold.” Dean winked and lipped his lips.

            “Great to hear, baby.”

            Benny clambered off of the bed and repositioned himself so that he was towering over Dean with his unzipped and exposed rock-hard crotch hovering over Dean’s orgiastic lips.

            “You ready, sugah?”

            “Fuckin’ get in me.” Dean growled before Benny’s cock was forcefully shoved into his opened mouth.

            Benny fully sheathed himself with the warmth of Dean’s moist throat and lips before he began thrusting his pelvis back and forth, in and out. Dean’s teeth lightly scraped the surface of Benny’s shaft with each collision; he felt the beginning taste of salty precum dribble on his tongue as the man continued to fuck into his face. He let his tongue roam and explore the meaty flesh of Benny’s cock during the seconds the dominant partner stilled for a period of time, both halfway in and out of Dean’s parted lips. Dean couldn’t help but quietly fuss over the fact that his own member was growing hard and stiff with arousal.

           The smooth texture of slippery muscle combined with the vibrations of velvety moans teased his cock repeatedly until Benny couldn’t take it anymore. With the urgent feeling of the possibility of bursting, Benny ripped his cock from the tepid haven of Dean’s mouth and quickly gripped his palm around its base. With a low groan and a hiss, Benny was uncontrollably cumming all over his lover, painting him creamy white.

           The feeling of Benny cumming on his chest perked his nipples and brought his cock to full attention. In no time Dean was splattering his own come overtop his own belly, adding to the whipped mess of bodily fluid. By the time both men were finished with their release, Dean was drenched in thick, gooey come.

           With both men panting, Benny repositioned himself so that he was seated behind Dean with his stomach supporting the younger man’s bound arms and back. They slumped into each other’s embrace lazily and left a moment to catch their breath.

           “We’ll have you shipshape in no time, darlin’.” Benny teased as he dipped his finger low onto Dean’s soaked belly and scooped up a glob of cum onto his finger before he stuck it playfully into Dean’s hungry mouth.

           “Mmm,” Dean sighed happily, “You can pillage my booty anytime.”


	4. Pour Some Sugar

**Summary for the Chapter:**

> Dean/Gabriel & candy fucking

**Notes for the Chapter:**

> Unbeta'd

                “Bend over.” Gabriel stated blankly from the desk chair he was swiveling in across the room.

                It had already been a long stressful day of classes for Dean, but he had made a promise to himself to persevere through the countless headaches and sleepless nights in order to study so that he could pass his finals. Def Leopard’s ‘Pour Some Sugar On Me’ was blasting through the hall outside of their room, along with the obnoxious metallic clicking noise which succeeded in breaking through the studious silence all thanks to the dorm’s lame attempt at an individual cooling system for each room on the wing, so he wasn’t certain as to whether or not he had heard his roommate—a.k.a. his fuck buddy for the school year—properly. He rubbed a hand over his face before he closed his textbook and in favor of looking over his shoulder took peer at his roommate which happened to be casually lounging backwards in his tie-dye swiveling five-wheel desk chair.

                Dean’s eyes caught the stare that Gabriel was aiming in his direction and then quirked his head and peaked his eyebrows. Dean couldn’t help but roll his eyes and laugh when he noticed Gabriel wasn’t saying anything in response to his questioning look, “Um, excuse me?” Dean pushed his chair away from the desk so that he was directly turned toward his roommate, “You wanna say that again? Maybe ask a little nicer?”

                Between his fingers, Gabriel was twirling one of those long rainbow-colored, hyper-sugar-infused lollipops you could find at any merchandise hut in an amusement park. The damn thing must’ve been a fuckin’ foot long, and Dean wondered why in the world a sane parent would buy that kindda poison for their kids to rot their teeth on. Gabriel had the lollipop resting between his thin lips while he pulled it in and out with an obnoxious slurping sound that caused Dean to cringe in disgust. Dean watched Gabriel’s lips with intent as the shorter roommate took one last drawn out slurp of the sugary stick and popped it out of his mouth with a devilish smirk, “I said bend over, hot stuff.”

                Dean just sat in his chair and gaped, “What the hell for?” He defensively crossed his arms over his chest.

                Gabriel, after placing the lollipop back in its wrapper, crawled out of his seat with the grace of a lazy house cat. He toed over beside Dean, bending himself just enough so that he could whisper in Dean’s ear while his fingers playfully massaged the aching knots in his hunched shoulders, “C’mon, baby, lemme show you a good time.” Gabriel’s hands roamed from the tops of Dean’s shoulders to snake down along the expanse of Dean’s chest before dipping under the thin fabric of his black AC/DC shirt to play with his nipples pebbling nipples.

                Dean frowned and shook his head, “No, Gabe, not tonight. C’mon, man, I got work to do.” He tried to weakly push Gabriel aside as he began wheeling his chair back toward the desk.

                Gabriel kept his place beside Dean, though, and continued to breathe into Dean’s ear, “Take a break from it, Dean. I know you’re tired.” Gabriel paused a moment to allow Dean to sit and contemplate the suggestion; he could see Dean’s own thought process  as his green eyes darted up to his forehead and he nodded a sigh—Gabriel knew he was going to get his way, “It’ll be fun, I promise.”

                “Fun for who? You?” Dean pouted, but Gabriel could see his roommate giving into the temptation of abandoning his schoolwork in favor of a sexual encounter.

                “I’ll show you a good time, Dean, I promise,” Gabriel winked, “Have you ever left my bed before without having a breathtaking orgasm? Hmm?”

                Dean’s cheeks heated with the rapid blush that appeared after Gabriel’s comment.

                “See?” Gabriel continued on to waggle his eyebrows, “Now let’s slip you into something more comfortable.”

                Gabriel began to tug at Dean’s cotton shirt, pulling it over and off his body before he kneeled down to take care of the blue denim jeans that were keeping Gabriel from licking at his absolute favorite treat in the room.

                Once Dean was stripped bare and waiting, Gabriel nudged Dean’s legs apart so that he could comfortably kneel between his thighs. With excited fingers, Gabriel wrapped himself around Dean’s semi-hard length and began to gently stroke up and down while adding a playful twist here and there. Dean released breathy moans and quiet whimpers as Gabriel tantalized his cock and balls with not only his fingers, but his fucking wet tongue, too. Gabriel was licking the underside of Dean’s cock, making sure to get every crevice soaked with spit as he licked and sucked. With his fingers scrunched in the strands of Gabriel’s slicked back, golden hair, Dean began pushing between Gabriel’s open lips, hungry for the wet warmth of his mouth. Gabriel could feel Dean’s seed leak and drip into the back of his throat, leaving a salty aftertaste behind. Before Dean could climb for full release, Gabriel pulled back and rose to his feet as he grinned down at Dean who was helplessly trying to rock himself back and forth into the cool, stale air of the room.

                “You fucker…” Dean growled as he started to wrap his own hand around his thick, crying cock.

                Gabriel smacked Dean’s hand away from his groin, eliciting a displeased hiss from Dean, “Ah, ah, ah, pretty boy. You gotta wait for the real fun.” Gabriel sauntered back over to where he had set his lollipop stick into its wrapper and grabbed it before he returned to stand in front of Dean, “Now bend over.”

                “No.” Dean glared unhappily up at Gabriel.

                “Do you wanna have fun or not?”

                Dean furrowed his brow for a second or two before he gave a short nod of his head, “Yeah.”

                “Then bend over.”

                Dean huffed but did as he was told, bending himself over with his elbows resting atop his desk and his ass sticking out and exposed. He only had to wait for a moment before he heard Gabriel walk up behind him. Dean felt Gabriel’s hand grab the area right above his hip bone before he felt something cool and sticky poke at his hole.

                “Dude. Lube. Use it.” Dean groaned.

                “You got the peaches, I got the cream, Dean-o,” Gabriel chuckled, “Plus I’m pretty sure there’s still some slippery remnants in here from when I fucked your ass straight through the beanbag chair two nights ago.” Gabriel stuck two fingers into his mouth before he pulled them out with a deafening suck and plunged them into the hole between the globes of Dean’s ass. Dean couldn’t help but whimper as he felt Gabriel’s slobbery fingers fuck in and out of him with rapid vigor.

                While Dean was too busy writhing and moaning on Gabriel’s very talented fingers, the shorter man took the stick lollipop in his mouth and started to wet its entire length with his saliva. When he felt the sweetening drool roll onto his tongue, he retracted his fingers and pushed the sugary treat deep into Dean’s hole.

                “Ahh, what the fuck!?” Dean’s breath hitched as he felt something unfamiliar slide between his cheeks; the object felt strangely ribbed and sticky.

                “Shh, got it all under control, babe.” Gabriel purred as he twisted the thin handle of the hard candy. He ducked his head down between Dean’s cheeks and started lapping at Dean’s now sickeningly sweet rim. Gabriel’s tongue teased in and out while following the rhythm of the lollipop.

                “Holy shit…” Dean panted as he clenched his eyes shut and threw his head back. His mouth was opened wide with a silent scream of pleasure dancing on the edge of his tongue. Dean continued panting while Gabriel pushed the lollipop in and out with quick twists.

                Gabriel, while feeling his own cock budding with interest, reached for Dean’s hand and angled it so that Dean was firmly holding the lollipop’s handle.

                “What the fuck, Gabe? Seriously? You’re fucking me with a piece of candy?” Dean’s words came out with heavy pauses between each breath as he fingered the handle.

                “Yeah, sweetie, why’d you think it felt so good?” Gabriel laughed, “If you wanna keep riding the high, then I suggest you get busy with your hand there.”

                Dean, the apparent king of huffing in annoyance, took Gabriel’s advice and started up the pace that Gabriel had previously set with twisting and tugging the stick in and out of his ass. He was able to hit the target several times, causing him to shudder and lose balance standing.

                While he watched Dean fuck himself on a rainbow sugar stick, Gabriel prowled around Dean to crawl onto the desk. He plopped himself in front of Dean and grabbed both sides of his roommate’s head to pull him down for attention. Dean reluctantly opened his eyes to see that Gabriel was sitting in front of him and pointing down at his own oozing dick. He took the hint and eagerly ducked his head down so that his plump lips could wrap around Gabriel’s hardness.

                Dean sucked down Gabriel hungrily while he franticly rammed the lollipop in and out of himself. Gabriel was clutching onto Dean’s shoulders for dear life as he felt Dean drink up his spilling cum.

                Gabriel’s voice was shaky from lust, “Thirsty?”

                Dean lifted his head up for a second and winked at Gabriel before diving back down for more.

                It wasn’t long before both roommates were sweating and shuddering with bliss, and were messily spilling their seed onto each other. Dean’s face was painted with hot white cream as he poured his own load onto Gabriel’s thighs that somehow managed to wrap around Dean’s bent waist. When their climax ended, both of them slumped back onto Dean’s desk and sighed.

                “Told you it’d be fun.” Gabriel snickered as he rolled his head to face Dean; he could see the lollipop handle still sticking out of Dean’s ass from where Dean was slumped over on the desk.

                “Fuckin’ candy…” Dean breathed.

                “Literally,” Gabriel deadpanned, “Speaking of which…” the shorter man stretched his arm over Dean’s back and pulled at the candy. The lollipop was dislodged with a wet pop and a throaty moan from Dean. Gabriel then proceeded to place the tarnished candy into his mouth.

                “Dude, that’s gross.” Dean stuck his tongue out and pushed at Gabriel’s shoulder.

                “Mm, tastes like virgin.” Gabriel teased.

                “Wrong flavor, dumbass.”

                “You’re right, tastes more like a needy cunt.” Gabriel laughed until Dean succeeded in pushing Gabriel completely off of the desk and onto the cluttered, cum-stained floor. Gabriel lazily looked up at Dean, whose face was hanging over the edge of the desk, “So, how do you feel? Pretty good, huh?”

                Dean stared into the distance tiredly before he turned his attention back to his roommate. With a glint in his eyes, Dean replied, “I’m hot, sticky sweet.”

                “From your head to your feet?” Gabriel waggled his eyebrows.

                “Yeah.”


	5. Just As Good

**Summary for the Chapter:**

> Fact or fiction? chubby!Dean/Sam/Cas (crack!fic)

**Notes for the Chapter:**

> Unbeta'd.

He didn't want to say anything. Actually, what he really didn't want was for _them_ to say anything.

  
Dean stared at his reflection in the body-length mirror as he attempted to squirm his way into his seemingly too-snug jeans. _How the fuck were these things not fitting? And wait a second, was that a muffin top spilling over the rim of his pants? Were those the fucking beginnings of moobs straining against the cotton of his shirt? **Shit.**_

  
Sure, maybe Dean ate a little too much chocolate and ice cream the last few days, but that was only because some crazed hag cursed him to live a month as a chick with a month long PMS issue. There was no way he could've gained that much weight.

  
Okay, so maybe it wasn't just a few days, but that was a very sensitive time for him, dammit. Dean never would've in a million years imagined that the effects of the curse would translate over to his real body, otherwise you could bet yer damn ass he wouldn't be touching more food than his usual diet constituted. Maybe he shouldn't have assumed that was the case. Y'know what they say about assuming things. Though it seemed more like the assumption was making an ass solely out of Dean... and a whopper-sized one to boot; he couldn't even believe how long it took to squeeze every last bit of himself into his jeans.  
With a defeated huff, Dean slumped his shoulders in defeat and marched out to face the judges. He was certain the second both his brother and the angel laid eyes on him, they'd roll over and die from a laughing fit, 'cause Dean knew damn well he must look absolutely ridiculous-- like trying to stuff a full Thanksgiving dinner into a toddler's lunch box.

  
He found Sam and Cas seated at the small table against the motel room's only window, focused intently on the research at hand. Nervously, Dean pulled at bottom of his shirt to help cover the slim pale sliver of flesh that was poking out from underneath. He cleared his throat.

  
Dean's interruption of the room's silence got the hunter and angel's attention as they both looking up questioningly at him.

  
"How are you feeling, Dean? Did the reversal spell work? Or rather, are you finding everything in working order?" Cas' gaze was curious but caring as he rose to his feet to stand beside Dean for further inspection.  
Dean felt his cheeks flush with embarrassing heat as he tried to speak, "Um... well, I actually wanted to ask you something about that."

  
"Of course, Dean, anything." Cas nodded.

Dean couldn't bring himself to open his fat stupid lips. He stood there awkwardly, too embarrassed to say anything about his current predicament. You'd think that telling his brother that he had a bleeding vagina would be harder than this ass-load of bullshit.

"Dean, are you okay?" Sam's tone was questioning and concerned.

Dean blinked his eyes shut and shook his head once before he got up the courage to speak, "Do I look fat?"

The room went dead quiet.

_Fuck. Fuck. Fuck._

Dean was too busy wallowing in his own mortification to notice that Cas' fingers were poking and prodding at his chest and stomach.

"It would appear as though your weight has increased from your previous norm." Cas concluded.

Dean could feel the beginnings of tears starting to gather in the corner of his eyes. _Wasn't this girly curse thing supposed to have ended already? Now he's stuck with an unwanted pair of moobs and moodiness? **Great.**_

Suddenly, pulling Dean out of his thoughts, he felt a soothing hand rubbing circles into the soft fabric on his back, "Hey, Dean, it's okay. Don't cry, please..." Sam's voice was calm and reassuring.

When Dean realized he was actually crying and not just tearing up, it caused him to bawl all the harder, "S'not, okay, Sammy. I'm a fat sobbing mess." Dean sank down to sit on the edge of the bed where Cas and his brother filled the seats beside him, "My clothes don't fit, I've got boobs and a double chin, and I can't stop crying!" Dean sobbed into his palms, "I'm never gonna get laid again!"

"Dean, just because you have some extra junk in your trunk doesn't necessarily mean it's a bad thing." Sam tried to cheer up his older brother, "I for one think you look fucking amazing like this." One of Sam's hands found it's way onto Dean's waist and began tickling away the stretch of clothing from Dean's pudgy midsection.

"Shut up, Sam, you're just saying that. There's no way anyone could find this attractive." Dean waved his at himself and stared down at his body.

"Actually, Dean, I would have to agree with your brother." Cas' voice was low and gravely and it tickled something inside of Dean, making his heart flutter and skip a beat, "Your appearance has taken on a softness that I find most appealing."

Dean looked at Cas with awe before turning to face Sam, who was staring at Dean with lust-filled hungry eyes.

"You've gotta be kidding me." Dean sighed before both Sam and Cas' palms crawled up Dean's chest to tenderly cup his chunky bits.

Kneading into the soft flesh of Dean's chest, both Sam and Cas gently eased Dean onto his back so that he was laying flat ontop of the bed. "Let us take care of you, Dean," Sam purred into Dean's ear, "We can make this so good for you."

Before Dean could make comment on what Sam was saying, he blurted in surprise when he found that Cas had started in unzipping and removing his pants, "C-Cas, what are you doing?!"

Cas looked up at Dean with a cool, sensual stare. The angel leaned forward just enough to rest the tip of his index finger on the swell of Dean's bottom lip to quiet him, "Shh, Dean. Not a word." The angel quickly went back to his business as Dean's snug pants were unceremoniously yanked away, revealing his thick, plump legs and ass to the world.

Sam quickly joined in and began tearing at the cotton shirt that covered Dean's chest. He tore from the center of the collar and pulled the fabric apart until a fine line of pale freckled skin was released between the split garment. Dean felt another flush of heat overwhelm his features and he couldn't help but feel nervous.

Without even noticing Dean's nervous discomfort, both Cas and Sam continued in kneading the older hunter's supple, doughy flesh. They licked and sucked and bit into every inch of Dean until finally he found himself relaxing under their encouraging touches.

If Dean was a cat, he would most certainly be purring.

Together all at once, they found themselves rolling Dean over onto his knees with his ass in the air. His head was at the foot of the bed, where Sam had come to stand in front of him, while Cas made his way to the head of the bed behind Dean.

When Dean heard the singsong sound of jeans unzipping, he couldn't help but salivate. Sam soon had his cock freed, ready and raring to go, leaking creamy tears at its tip. Dean could feel the blunt tip of Cas' hard cock brush along his inner thigh, and it sent shivers down Dean's spine and straight to his growing dick.

"Gonna treat you real good, baby. Watch you jiggle as you play on our cocks." Sam grinned as he dipped two of his large, meaty fingers into the space between Dean's peach-plush lips. Dean began sucking on Sam's fingers as he felt Cas begin teasing his hole with lubed fingers. He rocked back onto the angel's fingers, and then forward again onto Sam's fingers. He continued this motion for a minute or so until both sets of fingers removed and replaced hastily with large, aching cocks.

Dean didn't know which way was up by the time he was stuffed at both ends with Sam and Cas. He felt dizzy and warm, and oh so eager.

Sam lurched in and out of Dean's mouth, making certain to be gentle on his throat. Cas followed Sam's rhythm; everytime Sam pulled out, Cas would push in. Between the two of them, Dean looked like a spit roasted pig hanging on two cocks.

Cas grabbed hold of one side of Dean's hips and dug his fingers into the pliable rolls-- no, wait. Lovehandles. Cas' other hand reached down low to play with and stroke Dean's throbbing dick. Sam opted to keep one hand locked in Dean's hair while the other was lowered to play with the jiggling flesh of Dean's double chin.

"I love the way you look like this, Dean." Cas moaned as he thrust harder, "So soft and warm. And so very inviting..." Dean couldn't help but whimper with pleasure.

"Keepin' you this way from now on, Dean, y'hear? Eat all you want, baby. We love every inch of you." Sam hissed as he shot his seed into the back of Dean's throat. Dean tried not to gag on the creamy substance, and so he ardently began swallowing greedily.

A moment later, Cas' rhythm was becoming less calculated and more animalistic as he thrust harder and faster, hitting Dean's pleasure spot every time. After the first one or two clicks of the button, Dean couldn't hold himself back from coming hot and heavy all over the sheets. He slumped a bit, weak in the knees, but the angel held him in place as he worked his way further in until he found his own release flooding into Dean.

Both Sam and Cas pulled out at the same time with a wet, sticky pop. Dean rolled over and collapsed onto the bed. Sam and Cas enthusiastically followed him, and cuddled up next to him on either side. They nuzzled into his soft folds and rolls and tiredly purred into his neck.

Dean was roused from his tired haze when he heard Sam snicker. He peeked his eye open and glared over at his brother as if to ask what the hell he was doing.

"You've got a little something right there, Dean." Sam and Cas both teased.

Dean brought his finger to his lips only to find that his mouth was smeared with remnants of creamy white seed from when Sam had pulled out. Dean couldn't help but smile and lick at it like it was the sugary icing on a Krispy Kreme. _Heck, it tasted just as good._

The trio curled into themselves, dazed in post coital bliss. Dean wasn't sure if this thing with him and them was a curse all on its own, but he was in no hurry to find out. For now he would happily accept the sweet love gifted to him by the two best guys in his life.


	6. Habits

**Summary for the Chapter:**

> Prostitution + emotionally-numb!Dean.

**Notes for the Chapter:**

> Warning: thoughts of suicide and prostitution. Unbeta'd

                Cas disappeared. Sam left him. And Benny took a one-way ticket back to Purgatory. Everyone that ever meant anything to Dean got up and walked out ‘cause of all the lies and stubborn bullshit he couldn’t keep from spilling out of his pretty pink lips. He supposed he deserved the rejection to a degree.

                With no one by his side, he’d wandered the streets, hopping from town to town; bar to bar, in hopes of finding something strong enough to finally drown him and put an end to his misery. He’d run out of cash a few weeks ago, drinking away the last bit of change he had stored deep in his pockets.

                With no cash to his name, Dean had quickly become desperate. He needed to stay numb. He’s started to allow the abhorrent men that stalked the pubs and sex clubs he began to frequent stare when they approached him at the counter. He’d let them get a generous eyeful before he would take a glance at their wallets and see if they were worth the effort to butter up for some hooch and a fruitful romp in the bed.

                They’d use him up like a box of tissue paper, but Dean didn’t mind much. As long as he was stuffed with drugs or tripping over his feet ‘cause he’d had too much of the hard stuff, he didn’t have to think about all those sons of bitches that turned tail on him; he couldn’t feel all the messed up shit those smarmy dicks would do to him. He wouldn’t remember the nights when he’d begged on all fours like a good pet or that time when he was spanked by  his ‘daddy’ on the motel floor. He had to stay numb to keep them off his mind; he had to stay strong. When the soberness crept in, his silver bullets began to look like a tempting breakfast that he could jam straight down his throat with the help of a loaded trigger. But he’d abstained. Better a dick being shoved in his mouth than a gun muzzle.

                Until the day he saw those crystal-clear blue eyes pleading with him to come back, he’d keep going down this path. He’d keep getting caught up in the filth of society, drinking like a fish and getting fucked hard, begging for some cash to help get him by another day. Until he was wanted, he’d keep playing the ‘pretty boy’; keep letting strange hands abuse and use him until he got what he needed to stay locked in his haze.

                Until he was wanted, he’d keep being a nobody.


End file.
